Hydrochloric Acid → 5-(3-{4-Ethoxycarbonyl-5-methyl-3-[3-(4-methylpiperazin-1-yl)-propyl]-1H-pyrrol-2-ylmethylene}-2-oxo-2,3-dihydro-1H-indol-4-yl)-nicotinic Acid

HRID 1826795Notes

Reaction equation

[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:19]=2)[C:16]([OH:18])=[O:17])[NH:3]1.[CH2:20]([O:22][C:23]([C:25]1[C:29]([CH2:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)=[C:28]([CH:40]=O)[NH:27][C:26]=1[CH3:42])=[O:24])[CH3:21].N1CCCCC1.Cl>C(O)C>[CH2:20]([O:22][C:23]([C:25]1[C:29]([CH2:30][CH2:31][CH2:32][N:33]2[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38]2)=[C:28]([CH:40]=[C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][C:8]=3[C:11]3[CH:12]=[N:13][CH:14]=[C:15]([CH:19]=3)[C:16]([OH:18])=[O:17])[NH:3][C:2]2=[O:1])[NH:27][C:26]=1[CH3:42])=[O:24])[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-(2-oxo-2,3-dihydro-1H-indol-4-yl)-nicotinic acid (51 mg, 0.2 mmol), 5-formyl-2-methyl-4-[3-(4-methyl-piperazin-1-yl)-propyl]-1H-pyrrole-3-carboxylic acid ethyl ester (64 mg, 0.2 mmol) and piperidine (0.2 mL) in ethanol (1 mL) was heated in a sealed tube at 60° C. for 5 hours. The reaction was acidified with 1N HCl and the resulted precipitate was collected by vacuum filtration, washed with water and dried to give the title compound.

Workup

filtrationthe resulted precipitate was collected by vacuum filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-6e6f8ec4045349cfb1878a25bc087a52
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053086B2

Reaction notes

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